Potassium Carbonate → HCID 68911659, compound

HRID 1455284Notes

Reaction equation

HRID 1455284 reaction equation
[CH:1]1([C:4]2[C:8]([O:9][C:10]3[CH:17]=[C:16]([CH3:18])[C:13]([C:14]#[N:15])=[C:12]([CH3:19])[CH:11]=3)=[C:7]([CH:20]3[CH2:22][CH2:21]3)[NH:6][N:5]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1.CN[C@@H]1CCCC[C@H]1NC>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Cu](I)I>[CH:20]1([C:7]2[C:8]([O:9][C:10]3[CH:17]=[C:16]([CH3:18])[C:13]([C:14]#[N:15])=[C:12]([CH3:19])[CH:11]=3)=[C:4]([CH:1]3[CH2:3][CH2:2]3)[N:5]([C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)[N:6]=2)[CH2:22][CH2:21]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 24880657HCID 24880657, compound

Product 1

HCID 68911659HCID 68911659, compoundYield 4.4%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Copper iodide (13 mg, 0.07 mmol) was added to a solution of the benzonitrile of Example 4 (200 mg, 0.68 mmol) and potassium carbonate (197 mg, 1.43 mmol) in toluene (2 ml) in a Reactivial®. The reaction mixture was degassed, then 3-bromopyridine (79 μl, 0.82 mmol) and (1R,2R)-(−)-1,2-bis(methylamino)cyclohexane (20 mg, 0.14 mmol) were added successively. The reaction was then sealed and heated at 110° C. for 24 hours. The reaction mixture was then diluted with ethyl acetate (20 ml), filtered through a pad of silica and then washed with more ethyl acetate (15 ml). The filtrate was concentrated under reduced pressure and the crude product was purified by preparative HPLC to provide the title compound (11 mg, 4%),

Workup

  1. customThe reaction mixture was degassed
  2. customThe reaction was then sealed
  3. filtrationfiltered through a pad of silica
  4. washwashed with more ethyl acetate (15 ml)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-f13098bc6d7b47db87e4eb3646fce8c9
Source dataset
uspto-grants-2009_01
Patent number
US07482375B2

Reaction notes

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